THE APPRENTICE (Tom, Ms. Gray, and Marianne)
My name is Tom. The last few months of my life have been very exciting, since I graduated college. My BA is in business, and I’ll be getting my MBA in a couple of years, but in the meantime I took a job to pay my bills and build up some money for the future. I was able to land a spot with a good corporation, thanks to my grades and the influence of one of my instructors, and I’ve been working as an entry-level apprentice since June.
I guess I lucked out by going with this company, since they give me lots of good assignments and I’m learning a lot. The extracurricular activities are good, too. I never would have believed that people in business, the stuffy kind of people who run the corporations in America, could be so loose and so much fun. They didn’t have a course in school for me to learn that.
I work for several different bosses, in several departments. That can be tricky, since all of them expect the assignments which they give me to be done fast, and first. It takes some juggling to keep them all happy, but I’m getting pretty good at it. And all of them have included me in their lives outside of work, which is very exciting. They have very interesting lives.
My second week on the job was my initiation into the extra stuff. Ms. Olivia Gray, or Miss Ogre as we new hires call her, had been very pleased with some work I had done for her; she called me into the office and told me that I was invited to her place in the mountains for the weekend. There would be no work, just ‘fun and games,’ as she put it, and she winked at me. During the rest of the week, I was able to gather that none of the other new employees had been invited, so I had no idea who would be there.
She had given me a computer printout with directions to her place, and on Saturday morning I drove the two hours up into the mountain range east of the city. Down a long, tree-covered side road, I found her ‘cabin,’ which was actually bigger than most houses of people I knew. I had learned that she had been with the company for ten years, and it pleased me to think that this was the sort of thing I had to look forward to if I were successful.
I parked and walked up the stairs to knock on the door. Ms. Gray came to open it, dressed in a sweater and slacks which made her figure look even better than it did in the power suits she wore in the office. She ushered me into the spacious main room of the house, and we sat on the couch. “Am I the first one here?” I asked.
“What? Oh, no, there’s no one else coming–today,” she said, “This is just a chance for me to get to know you better–and for you to know me.” She smiled warmly, and I thought for a fleeting moment that I was in for a really good time; but this was Miss Ogre, and I doubt that she indulged in the sort of things I was imagining. “Does our being here alone bother you?”
“No ma’am . . . I’m just surprised. I thought it was going to be a kind of house party.” I smiled back at her.
“Well, it is. A house party–with only two in the house. You’ve done very good work in the short
time you’ve been with us, and I wanted to reward you.” She was looking at me very intently.
Now I was wondering whether or not she did indulge in the sort of things I was imagining–and imagining very vividly as I looked back at her in what I hoped was just as intense a way.
“I’m very grateful, and glad to be here. I enjoy working with the company. I–don’t misunderstand my meaning–I enjoy working for you.” I blushed, afraid she would think I was sucking up to her. “I hope you don’t think I said that just to suck up to you,” I said, putting my thought in my mouth.
“No, I know you’re your own person, I’ve observed that about you. I invited you up here to . . . well, to suck up to you.” She smiled wickedly.
“Why would you have to do that? You’re an executive, and I’m . . . nothing, really,” I said. What in the hell was she talking about?
“You’re not nothing. You’re a very attractive young man, and I am occasionally attracted to attractive young men. Perhaps I mis-spoke; I invited you up here to suck you. There, I can’t say it more clearly than that, can I?”
“Ms. Gray! I’m not sure what to say. I don’t want to do or say anything that would offend or hurt you.”
“The only thing you could say that would hurt me would be ‘goodbye.’ And there’s nothing you can do to offend me, except to say that you have no interest in me, or in my body.”
“No-o-o-o, I can’t say that. Although the thought never really entered my mind until a minute ago.” I was really out of my depth here.
“That’s good! All business at the office. But we’re not at the office now. Tom, I want you to kiss me, just the way you would kiss any woman.” She moved closer to me on the couch.
I put my arms around her, and kissed her mouth tentatively. “You must be no fun on a date,” she said, and smiled. “Really kiss me, Tom.”
And I did. I pressed my lips against hers and gave her the best kiss I could, holding her body tight against me. I could feel my erection rising rapidly. Then she took one of my hands and moved it under her sweater onto one of her breasts. I felt my hand touching a soft, warm breast, and felt the nipple raise under my palm. I was amazed that she wasn’t wearing a bra, and was pleased to realize that I hadn’t known it while looking at her before.
We continued kissing for a couple of minutes, and then her hand began caressing the front of my pants. She rubbed my erection, and then whispered “I want to see it.” I let go of her and reached down to unzip my fly. My cock leaped out of the opening, and she quickly closed one hand
around it. “It’s beautiful,” she said. “Stand up.”
I stood on shaky legs, and she undid my belt and pulled my pants down. Then she lifted the band of my shorts up and over my erect cock and let them fall at my ankles. “Beautiful,” she murmured, and leaned forward to put her mouth on my shaft and begin sucking. Her hands went around behind my buttocks, and her fingertips caressed the crack of my ass as she pulled me into her mouth. “Mmmnnn,” she moaned.
I grasped her head and began fucking into her mouth in earnest. I was no longer in awe of her as my boss, and I was determined to enjoy this entire experience as much as possible. I thrust again and again, and we found a perfect rhythm as she sucked down on me each time I pushed my cock forward. Then I felt the surge that meant I was going to cum. I shot semen into her mouth, probably more than I had ever produced before, and she moaned as she swallowed two or three times to get all of the fluid which was pumping out of me. When I was drained, she stopped, took her mouth off me, and began kissing up and down the length of my shaft.
“That was wonderful. Perhaps sometime I could do the same for you,” I said. She looked at me in disappointment, and I said “Just kidding. I know you probably don’t want that.” I was enjoying this. She pouted up at me.
“I had no idea you were so droll,” she said. “Maybe I’ll let you do that, and maybe I won’t.” She stood, and started pulling her slacks down her thighs. I marveled at her legs and her flat belly, and reached forward to pull her panties down. “I think you’ll let me do it,” I said. She whipped off her sweater, and said “Oh, yes, do it, do it, do it,” and lay down on the couch with her legs wide apart. I knelt between them and looked down at her sopping slit, lowering my face until my lips were kissing her mound and then her belly.
“Eat me, Tom, please,” she begged, and I moved my mouth down to put it on her eager pussy. She rammed her hips upward into my face, and my tongue went an inch inside her. She bucked and moaned and writhed on the couch, and I licked her to an orgasm in less than a minute. She
lay whimpering as I dutifully licked up as much of the fluid as I could get to. She smiled at me.
“This is go
ing to be quite a weekend,” she said, and pulled me by the hand down the hall to her bedroom.
Ms. Gray and I made love three times that evening and into the night, stopping only to go out to the kitchen and make some dinner. I fell asleep with her in my arms, and awoke early to hear the murmur of her voice in the living room. I got up and went out totally nude, finding my clothes in a neat pile on the couch. I slipped on my shorts just as Ms. Gray was finishing her call.
“I was calling a friend of mine. She was supposed to come up today, but she held off until I called her. Now she’s coming.”
“Ah. Would you like me to clear out?” I asked.
“No, no. She was reluctant to come because you were an unknown quantity. I just assured her that you were a delight and that she should get up here and enjoy the fun.”
“Enjoy the–is that me?”
“Yes, Tom, that’s you. My friend and I share men together, but she wanted to make sure you were worth her time. She’s very particular.”
“And you gave me a passing grade?” I asked, teasing her.
“Yes, just barely passing. An A but not an A+.”
“An A is passing? You are a tough grader.”
“Anything less isn’t worth her time, or mine,” Ms. Gray said. “I guess we’re both very particular.”
“What does she do? For a living, I mean,” I said, grinning.
“She’s an executive also. We went to college together, and we’ve been doing things together ever since.”
“With men,” I said.
“Or with each other if there wasn’t a high-grade man around. And with other women. We’re very liberated.”
“I guess. This is outside my area of knowledge, you know.”
“You wouldn’t turn down the chance to watch two women make love, though, would you?” She was giving me that intent look again.
“No, I wouldn’t,” I said. “What’s her name?”
“Marianne. She’s really a nice person, and I think you’ll like her. She’ll be here in another hour, but in the meantime let’s you and I go for a walk in the woods.” And we did, coming back to the house just before the hour was up.
“I’m going to get in the shower, if that’s okay,” I said.
“Okay,” she said. I went in and began showering, starting to think what the next few hours might hold. I imagined what Marianne looked like, and also imagined what it would be like to be in bed with two women. I’ve never had that chance.
The more I thought about it, the bigger my cock became. Ah, well, I thought, this way I can wash it really well. I began stroking it holding the soap, and the viscous bubbles made my hand slide easily up and down the swelling shaft. I moved the soap under my testicles, and back into my ass, washing myself thoroughly. My eyes were closed, and I was enjoying the shower immensely.
Suddenly the glass door of the shower opened, and Ms. Gray was standing there next to another woman. Also in her thirties, she was even better-looking than Ms. Gray, who is very lovely.
“You–you must be Marianne,” I stammered, taking my hand away from my genitals.
“And you must be Tom,” she said, smiling. “Olivia, you weren’t kidding; he’s beautiful.”
“Ah, shucks,” I said, pretending modesty. I know I’m good-looking.
“Would you go back to what you were doing? I enjoyed watching you,” she said.
“I’ll leave you two alone to talk,” Ms. Gray said, “while I go slip into something naked.”
I reluctantly began stroking my cock again with the bar of soap in my hand. “It’s been a long drive,” Marianne said. “Do you mind if I join you?” Without waiting for an answer, she began undressing. I was treated to the sight of the loveliest body I’ve ever seen. Her breasts were firm, and the way her hips and her belly met were special; I felt my erection getting larger in my hand. When she was nude, she hopped into the shower and closed the door. “Can I borrow the soap?” she said.
I handed it to her, and she put it up to her face and began smelling it. “It smells even better now,” she said. Then she put it in her mouth! She leaned against me, and her other hand closed around my hand on my cock. “Why don’t you let me do that,” she whispered, and my hand fell away to the side. “Don’t waste it; put it somewhere,” she said huskily, and I reached up to cup one of her lovely breasts. Her hand was stroking me slowly and lovingly, and she put the soap in my other hand. “Wash me, will you?” she asked.
I ran the soap over her body. I did her shoulders and neck, then her back. I moved the soap around to rub over her belly, and then slipped it down to her hair-covered mound. She spread her legs, and I moved the soap in to wash the lips of her pussy. She leaned against the side of the shower, letting go of my swollen cock, and said “do my ass.” I pushed the soap between the perfect globes of her ass, and rubbed it on her anus One of her hands went between her legs, and 6
she began stroking herself. I put my other hand on her neck to hold her in place against the wall of the shower, and then inserted the head of my cock in the crack between her cheeks instead of the bar of soap. She moaned, and said “Yes, do it. Fuck me there.” And for the first time in my life, I was in the ass of a woman, only an inch or two at first and then almost the entire length of the shaft as the soap acted as a lubricant. I pumped into her again and again, and was very close to an orgasm when she pushed back against me and said “Stop. For now.”
She turned and clutched my cock again, rubbing it clean in the streaming water. Then she knelt on the shower floor and began sucking me off. I was furiously fucking into her mouth when Ms. Gray pulled the door open and said “hey, you two, I’m feeling very lonely out here.”
I sheepishly pulled my cock out of Marianne’s mouth, and stepped out of the shower to grab a towel and dry myself off. Marianne came out also, and cuddled up to me inside the towel; so I dried both of us off. “You’re a lot of fun,” she said.
We went into the bedroom, and Ms. Gray motioned to me to get on the bed. Then she said to Marianne “go back to what you were doing. I just couldn’t see it well because of the steam.”
Marianne straddled my thighs and went back to sucking on me. I watched her eagerly for a moment, and then Ms. Gray swung herself over my shoulders and lowered her pussy to my face. “You’re enjoying looking at that too much. Look at this.”
I looked up at her beautiful snatch, the dark curly hair masking the open slit. She moved up a bit, and her pussy was an inch above my nose. I put out my tongue, and she lowered herself onto it. “Ohhhh,” she moaned, “eat me, eat me, eat me.” I licked and slurped over every inch of the lips of her pussy and the inside of it as far as my tongue would go. I could feel Marianne’s mouth working on my cock, and her hand was fondling my balls. I shot into her, pumping again and again as the fluid ran out of me. Ms. Gray came just then too, drenching my lips and my cheeks with the honeyed fluid from her pussy.
She moved away from my face, and lay down on the bed. “Marianne, come up here and let me eat you,” she said. Marianne moved up the bed and straddled Ms. Gray’s head, pressing her eager pussy down onto the other woman’s mouth. She looked over at me laying there, and smiled; my cum was still rolling down her chin, and she used one finger to catch it and then put the finger in her mouth. I quickly got up and knelt next to her, holding her by the shoulders and kissing her. My tongue went into her mouth and retrieved a lot of my own fluid. “Yes, you’re a lot of fun,” she said, just as a long, shuddering orgasm caused her body to tense.
For the next few hours, we touched and fondled each other, and about three o’clock I was treated to the sight of two beautiful women eating each other ou
t. They were very efficient and expert, and each of them quickly climaxed in the mouth of the other. Marianne collapsed on the bed on her belly, and then saw
my reawakened erection. “Why don’t you put that where it was in the shower?” she asked. Ms. Gray looked perplexed, since she had come into the bathroom just as Marianne was sucking me off; but her eyes widened as she saw me climb over the prostrate form 7
of her friend and place the head of my cock against her ass.
“Marianne! You let him do that?”
“Yes, and he does it very well. I know it’s not your cup of tea, Olivia, but I’ll bet you’ll watch.”
And she did watch as I spit on my cock and inserted it into her friend’s willing ass. I was in almost all the way, and began a slow fucking that brought moans from Marianne and gasps from Ms. Gray. She moved in close to get a good view of my cock pushing in and pulling out of Marianne’s anus, and her hand reached between my legs and began caressing my balls. Her other hand went under my cock and began fingering her friend’s slit. Marianne was kneading her own clit, and it was only a matter of a few minutes before she came with a flood of fluid which soaked the bedcover. I shot into her ass at almost the same moment, draining my body of its juice. I collapsed on Marianne’s back as her knees straightened out and she lay flat on the bed.
“That–that was something to see,” Ms. Gray said.
“It was even better to experience it,” Marianne said. She looked back at me. “Olivia has never had that done for her. It’s just a personal thing, I guess.”
“You can only do what you can do. I’ve never done that before today myself,” I said.
“You mean I got a virgin? How exciting. You do it very well for a beginner.” She smiled at me.
Olivia snuggled up next to us, and her hand caressed my ass. “I just think it would hurt too much,” she said. “But it did look like fun.”
“It does hurt–at first. But once you get past that, it’s a real pleasure to feel a cock in there and know you’re giving such pleasure to a man,” Marianne said.
“I’m sorry if I hurt you,” I said.
“Oh, you didn’t. I just meant it hurt me the first time. A long time ago. I’ve been fucked there by a lot of men; they seem to like to do it. And they like to put their tongues in me too. You have some new experiences ahead of you, Tom.” I was startled. I had never thought about such a thing, while I had thought of fucking a woman’s ass since I was about sixteen. I guess my education isn’t quite complete.
“Tom, if you ever do that for her, I want to watch that, too,” said Ms. Gray. Then she smiled wickedly. “You can watch me do it sometime, if you want. Now I’ve done that.”
“Yes,” said Marianne, “and I’ve done it for her. I just don’t think we’ve done it with someone
watching.” She giggled.
The conversation had caused me to get another erection, improbable as that sounds. It’s good to be young. I got to my knees from where I was laying on top of Marianne, and Ms. Gray looked approvingly at my hard cock waving in the air. “Bring that here,” she said, and I got off the bed to stand by her prostrate body as her head came up to cover my swollen knob with her mouth. I pumped into her for a couple of minutes, but didn’t cum.
In the evening, we made dinner and sat around the table like old friends talking and laughing. Someone coming in would never guess what had transpired all that day in Ms. Gray’s big bed.
After dinner, I loaded my stuff in the car and said goodbye. I drove off with the two of them on the porch, their arms around each other’s waist, smiling broadly. Monday morning at the office was going to be very interesting.
2 (tom and wendy)